Sex work is a controversial and polarized topic, and there are many perspectives on it. My position is complex — but for me, when it comes to how we actually interact with sex workers, one important factor is whether they enjoy their jobs. I am absolutely in favor of giving better options to sex workers who do not enjoy their jobs, and I am horrified by the idea of a person being trafficked or coerced into sex that they don’t want to have. But I also know people who have sex for money 100% voluntarily, and I do not want to deny their experience.

My friend Olivia, a 25-year-old graduate student, recently started advertising her services on a “Sugar Baby” site called SeekingArrangement.com. I think it’s important for more people to understand these kinds of experiences, so I asked to interview her. Many people have pointed out that once a person starts thinking about the definition of “prostitute”, it’s a bit difficult to define what exactly a prostitute is. Some of my sex worker friends have asked the question: what exactly is the difference between a person whose partner buys her a fancy dinner after which they have sex — and a person whose partner buys sex with money? Olivia has thought at length about this, and I’m grateful to her for sharing her perspective.

Please note that Olivia is exceptionally privileged. What you are about to read is a portrait of what the sex industry looks like for a person who is very privileged: she comes from a white upper-middle-class background, she is not desperate, she is being paid a lot of money, she does not have a drug addiction. Many other peoples’ experiences in the sex industry are different.

The interview went long, so we posted it in two parts. Part 1 is available if you click here. In Part 1, Olivia told us that she usually uses the site SeekingArrangement.com to find clients; she described the nature of a “sugar baby” site, and she talked about some things she’s learned about gender roles. Now for part 2:

Clarisse Thorn: In Part 1, you mentioned that you feel powerful in your relationships with these men. But there are issues of your safety, right?

Olivia: I think there are issues of safety anytime a person meets someone they don’t really know, especially if they plan to spend time in private. And especially if you’re dealing with topics as sensitive as sex or money. There may be more issues of safety with this because some people really do believe that money can buy them anything. But for the most part, when I meet people they seem very respectful.

Things I do to increase my safety are that I tell my husband and my friends where I’m going to be, I tell them exactly where I am. I’ll do things like take down a client’s license plate number and text it to my husband. I’ve been thinking maybe I should look at each client’s driver’s license too, and text the client’s name and driver’s license number to my husband. I think some clients might feel threatened by that, though.

The most important thing for my safety is that I’m willing and able to walk away from situations. I’m not desperate — I won’t starve or die if I don’t do this work. I meet all my clients in public first for a meal, and if someone sketches me out, I leave. I’m not so desperate that I’ll get into a situation that scares me.

I guess I am at risk if I meet a really crazy person who wants to chop me up and put me in a dumpster. But I could meet a person like that during a normal night at a bar, too.

The major risks that I see include that I might catch an STD — but I use protection. I might end up alone with someone who believes that the money he’s paying actually gives him the entitlement to do whatever he wants to my body, but I’ve never encountered anyone like that. The thing is, as I said before, I haven’t met anyone who I think would actually describe themselves as paying for sex. The terms on which I continue to see these men are probably less explicitly negotiated than an escort’s terms would be. I don’t have flat rates, for example.

I’ve heard escorts complaining that people who use sugar baby sites are unprofessional, and I think that from an escort’s perspective they probably are.

Clarisse Thorn: If people are unwilling to actually talk about sex for money, it must be hard to negotiate your encounters. Do you have a set of steps for negotiation?

Olivia: I haven’t been doing this for very long. It’s varied so far. Usually, I meet them for some kind of meal, and we chat. We have a perfunctory conversation, like — “How was your day?” Then one of us will say something like, “Tell me a bit more about what you’re looking for. Why are you on the site?”

Then we’ll explain our deal to each other. Like, he might say: “I’m divorced, I’m looking for companionship.” At some point, money comes up. I am always extremely vague when I talk about money. I’ve found a good deal of variation in how squeamish people are about money.

For example, one client was saying that he wanted to get married again, but not yet. I said, “Huh, well, if you’re interested in a more emotional relationship, how do you feel about involving money?” The way he explained it to me was that people are attracted to each other for all kinds of reasons, probably including money, so why not be up front about the fact that money is attractive. He seemed almost confused about why I asked. With that guy, I ended up sleeping with him before we even talked about money — which was a huge risk, but I thought it might work, and it did. We had the money conversation immediately after we had sex — at some point when we were taking a break, I asked what he was looking for more specifically from this relationship, and he said that he wanted to see me again, maybe once a week. I think I asked him his preference for a monthly allowance as opposed to every time we meet, and he said he’d rather do something monthly. Then when we were getting dressed, he pulled out $1000 cash and handed it to me, and said, “I’ll give you the balance next time we see each other.”

With other people I can be more straightforward. Maybe they aren’t sure how to set up the relationship, so maybe I talk about another client, like: “I have another client I see 3 times per month for $3000,” and they might say, “That sounds good.” But some guys will just negotiate it per encounter. One guy brought it up very quickly after we’d exchanged some emails. He said that he prefers to do a “per meet” of $300 — he called it a “per meet” — I told him that was too low and quoted him $1000, and he said he’d meet me in the middle. Another guy told me that he would just slip $400 into my purse when he saw me, and that’s exactly what he did.

I have one client I’ve never explicitly discussed money with at all. I had lunch with him, and we didn’t negotiate anything, though we talked a little bit about our reasons for being on the site. The next time I saw him — we were deciding where to meet, and he asked if he should get us a room. I said that I would like that, so I met him and we had sex. He knew it was my birthday soon, so as we were getting dressed, he said, “I know we haven’t talked about money, so I got you some birthday spending money,” and he handed me an envelope with $400. The next time I saw him, he asked about my plans for the evening. I said I was having dinner with a friend, and he handed me $400 in an envelope and said, “Maybe this will help pay for it.” I’m lucky that I’m willing to accept $400 — it’s my lower bound, but I’m willing to accept it. Imagine if I hadn’t been willing to take $400 — that would be super awkward. Probably I should have negotiated that situation more clearly, but it worked out okay.

I’ve heard about situations where unclear negotiations did not work out okay. There was a “New York Times Magazine” article about the site published in 2009. In that article, there were some examples of unclear negotiations that didn’t work out well. But it sounded like that woman didn’t really know what she wanted, and didn’t really enjoy the work. But I do. And I know other women who do, too.

I have a new client who paid me $3000 up front to see me 3 times a month. But I haven’t heard from him since our first meeting. If I were his girlfriend, I’d call him, but he asked me not to call him. So I don’t really know what the deal with that one is. Maybe he’s gonna flake out on me, but he already gave me $3000, so that would be weird.

Clarisse Thorn: So, your husband. You mentioned him briefly. How does your husband feel about this?

Olivia: He does not seem particularly threatened. We already have an open relationship. I think he sometimes feels very visceral jealousy, but that’s just like any other time one of us has sex with somebody else. We just have to talk about it.

Part of the deal here is that I’m doing this because I’m broke. My husband really wants to be able to support me financially, but he can’t right now, so I’m supporting both us doing this. I think that’s a real blow to his ego. To the extent that he gets bothered, I think it’s because I’m allowing other men to support me and give me money; he doesn’t care about the sex. Even though I see this as work, he sees this as “here’s this rich successful guy who just gave my wife a bunch of money, and she slept with him — so probably she’s attracted to him.”

I am kind of attracted to my clients, and I kind of get off on making them happy, and I happen to think that the age difference is kind of hot. I like having sex with them; it’s not unpleasant. I like hearing about these guys’ life stories. I think it’s interesting. But these guys would never be a threat to my husband. I would never be sleeping with any of them except for the money. And I love my husband. I’m always very up front about the fact that I’m married and I love my husband. My clients accept that.

I’ve heard escorts complaining that people who use sugar baby sites are unprofessional, and I think that from an escort’s perspective they probably are.

I found this comment particularly intriguing, and wondered about the social/economic/status dynamics that clearly underpin he definition of “professional”.

The description of the varied means of negotiating appropriate recompense sounded to me like an incredibly skilled and professional craft or art – akin to diplomacy and other subtle language forms. Not least, making the pitch on the right communication level of explicitness or implicitness, and still making sure that it’s understood.

It ends up sounding like yet another variant of, “At least we’re not like those people!” which seems to plague sex work in various ways. This time, it seems to be something about class in terms of business model?

Well, when talking in terms of work, “professional” tends to be seen as the pinnacle – middle class as opposed to the working class “tradesmen” (or tradespersons). Calling someone “unprofessional” usually indicates a belief that their working practices are substandard or that their set-up is poorly managed. So the implication from the quoted passage seems to be that escorts are saying to sugar-babies, “you are slapdash and shoddy, whereas we are quality and high-status.” Escorts are saying of their own working practices, “At least we are not like them.”

I know that you wrote that Olivia is exceptionally privileged, but I just can’t get past this part. If you’re anywhere near the ability to command a one-grand-a-night fee, you ain’t broke. And if you think that the word could even remotely apply, you have absolutely no idea what broke is.

Saying that, it’s like that annoying as hell Allstate commercial, the one with the line about being on a “Ramen noodle a night” budget. Anyone who’s lived on that kind of diet knows the following fact.

You’re not choosing Allstate. You don’t have a damn car.

So, yeah. Broke? Not in the effin’ least. At worst, you got yourself a cash flow problem.

She means that she was and would be broke outside of the black market. I guess you can say her youth, beauty, and location are assets, but converting those into cash is a little more complicated than making an appointment with an accountant.

I’m well aware of the fact that sex work involves more complicated conversions than working with accountants. (Though, granted, my experience with the latter is primarily through knowing a sex worker who later became an accountant.) My point is that if a person is in the position to be getting that amount, they much more than likely have access to a certain baseline when it comes to shelter, diet, hygiene, medical care, clothing, etc.

Which is above and beyond that accessible to a person when they’re broke.

Also, about the whole “not qualified to call herself broke” thing, this immediately came to mind;

Olivia: “The most important thing for my safety is that I’m willing and able to walk away from situations. I’m not desperate — I won’t starve or die if I don’t do this work.”

…and then, later…

Olivia: “Part of the deal here is that I’m doing this because I’m broke.”

Obviously, you can be broke and still not be at risk of “dying” or “starving”, but…. I’m inclined to believe that she doesn’t really understand the definition of “broke” because of these two statements, either. She is in a very, very privileged position indeed when it comes to sex work.

However, I guess Clarisse already DID mention a disclaimer that in no way does her friend’s position reminiscent of most other sex worker’s positions, so I should perseverate, but… I digress. It feels to me like she has a very me/them position when it comes to how all of those other, “unprofessional” sex workers are that it seems a little bit arrogant to me for some reason that I can’t pin down.

@Sherry — It feels to me like she has a very me/them position when it comes to how all of those other, “unprofessional” sex workers

To be clear, at one point she said that she’s heard that escorts consider sugar baby sites to be unprofessional. But she hasn’t called other sex workers unprofessional; she’s said that she thinks that some sex workers would consider her to be unprofessional.

@machina — I don’t see how this is a “blurred edge” of sex work, it seems to be providing sex for money.

Sure. Except that her clients specifically don’t want to think of themselves as hiring a sex worker, and some of them won’t even talk about the fact that they’re paying her for sex. So how different is it from, say, what people might talk about as a “gold-digger”?

@Snowdrop — The description of the varied means of negotiating appropriate recompense sounded to me like an incredibly skilled and professional craft or art – akin to diplomacy and other subtle language forms. Not least, making the pitch on the right communication level of explicitness or implicitness, and still making sure that it’s understood.

I’ve thought about this a lot (as has been reflected in much of my writing and many comments on this blog!) … I have to say that Olivia is one of the more skilled social maneuverers I’ve seen. In general, her social skills are just above and beyond most people’s. Part of me wants to tell her, “Man, you are taking some serious risks here, both with safety and with your financial negotiations,” but on the other hand, she’s better than me socially, so maybe she’s not taking as big a risk as I think.

Well people are often squeamish about hiring any form of worker privately at a negotiated price. I’ve had people being squeamish about hiring cleaners or yard workers. There can be a little dance performed around these things, but in the end labour is performed for money.

I don’t know how to compare this to “gold diggers” without knowing what their arrangement is.

Olivia emailed me this morning saying that someone on the site messaged her and when she looked at his profile, here’s what it said in the money section: “I am not a ‘sugar daddy’ to be led around by my big wallet… I can provide in other ways.”

Having worked as both a prostitute and a sugar baby I found this article to be extremely fascinating. It echoed a lot of my own experiences.

I think one reason escorts call sugar babies “unprofessional” is that for the most part, they don’t describe what they do as a job or profession, but rather as a different structure of dating or relationships. Even though on Seeking Arrangement you’re still doing a lot of the work you would as an independent escort (photos, copy-writing your description, negotiating clients… ect.) you’re doing so under the explicit premise that you are NOT a professional. It’s a delicate line of marketing yourself as someone genuine who would never market their sexuality. At least that was my experience. Many sugar babies are also fiercely defensive about not being prostitutes, and belittling to those who identify as such. It can be grating when your job descriptions feel extremely similar. Much like pro-Dommes and strippers, some sugar babies identify as sex workers and some adamantly don’t. So at least some of the “unprofessional” language is self imposed I think.

Reading about the negotiations was almost painful. That was the exact reason I switched to more standard escorting. It was far more predictable. I knew exactly how much I charged per hour and negotiations about time and money had to be direct and upfront. I felt far more in control. The line of having sex and being paid, but “not being paid for sex” was also a hard one to straddle comfortably for me. I know others who thrive on it, but it was emotionally exhausting.

@Infra: A person who is taking in that much money absolutely can be broke. I don’t know if this applies to the woman in this article, but one way someone could find themselves in that situation would be due to medical bills. Or perhaps they were in an economically privileged position once, but have since lost their job, yet still have the same bills as before.

Please try to consider situations beyond the obvious. This may not apply to Olivia, but if we’re discussing sex work in general, it could apply to many of the women we’re talking about.

Anonymous, I understand what you’re getting at, but I think that this probably relates to different experiences of poverty. “Broke,” to certain people, definitely means a lot more than not having liquid assets, or even being seriously in debt.

But I’m not presuming that you’re unaware of this. You might be one of the people who’s been broken down to that level through having to deal with long-term cancer care, after medical insurance stopped covering it; or who lost everything to storm or fire and had nothing and no one to fall back on. I mean, even with what I’m living on now, being on disability (which still places me about two grand under the poverty threshold), I still consider myself to be *far* better off than where I was at when I was broke.

I’m not washing my hair with Dial because I couldn’t afford or get shampoo that week. I’m not timing my grocery shopping on one day of the month because that’s the one day that the bus fare works out to “free.” I’m not letting my clothes sit in the washer for an extra hour waiting for the right dryer to open up at the laundromat so that I can save myself an extra buck in quarters. I’m not wagering whether or not I can get away with wearing those jeans a fifth day before washing them so that I can save that buck in the first place. I’m not buying clothes from the discount rack at the second-hand store only two times a year. I’m not living on seasoning bacon or recycling coffee grounds. I’m not turning on the heat only when the temp drops below 40 degrees.

(Course, that was still better than when I was homeless.)

So maybe we’re going on very different definitions of what “broke” means. But that should clarify why I wrote what I did, above.

It’s just that after certain experiences… the meaning of that word becomes very, *very* important.

After thinking about it a bit, there might be a concise way to restate that last comment, I guess that the best way to put it is this:

When it comes to a word that signifies being penniless, maybe it’s worth considering weighting its use toward the experiences of those who live with that condition, and not toward the results of the balance sheet. I don’t say that to trivialize the latter, or the very real risks of that condition, to self and loved ones; although I’m sure that I haven’t carried the raw amount of debt that others have (I haven’t owned a house, for example), I’ve carried my share, and I’ve been caught under its weight when the floor fell out. But experiences need their languages. They need their words and their voices, and when things get used too broadly, words get weakened where their power is needed. Where expression and impact and the ability to cause change is lost without them.

As I see it, from my and others’ experiences: “broke” is one of those words.

Honestly, I don’t know anyone in real life who sees using “broke” to mean anything less than completely destitute as an offensive sign of privilege … I also know people who regularly say things like “I’m starving!” when they’re very hungry. (I did this once when I was in Africa, and then I felt like a total asshole.) I personally refer to myself as a “starving artist” frequently, with some degree of intended humor. I guess this is something I should examine.

In terms of Olivia specifically, my understanding is that she owes quite a lot of money for graduate school, and she and her husband don’t have any real income stream right now other than sex work. They were significantly behind on rent and were concerned about eviction before she took up sex work.

One thing that’s useful in understanding the issues involved here is the differend.

I do want to say, though, that the appearance of my reaction to the contrary, I’m not unsympathetic to Olivia’s situation. I wasn’t in graduate school, but I did face a somewhat similar situation, as have friends; it’s one of the reasons why I became a driver and got involved in other aspects of the industry for a while.

I did want to come back here and say myself that I am sympathetic to critiques of Olivia’s perspective as it’s presented here. I wanted to interview her because I thought she had an interesting viewpoint and a lot of good thoughts on these topics, not because I think she’s perfect. I can see a little bit of arrogance in how Olivia approaches this topic, and frankly I am a little bit worried for her in terms of how she’s negotiating some of this stuff. On the other hand, I think it’s really important for me as an interviewer — and for anyone who’s dealing with a marginalized group like sex workers — to allow people to report their thoughts and feelings in their own words, without overt pressure to think differently.

About Clarisse

On the other hand, I also wrote a different book about the subculture of men who trade tips on how to seduce and manipulate women:

I give great lectures on my favorite topics. I've spoken at a huge variety of places — academic institutions like the University of Chicago; new media conventions like South By Southwest; museums like the Museum of Sex; and lots of others.

I established myself by creating this blog. I don't update the blog much anymore, but you can still read my archives. My best writing is available in my books, anyway.

I've lived in Swaziland, Greece, Chicago, and a lot of other places. I've worked in game design, public health, bookstores, and digital journalism. Now I live in San Francisco; I make my living as a media strategist, editor, and writer.